Ready to Start Your Side Hustle? Read This👇
How to improve your odds of entrepreneurial success
⏱️ Reading Time: 5 Minutes
TL;DR
- Entrepreneurship isn't magic; it's a skill anyone can learn.
- Still, many budding entrepreneurs struggle because they haven't had opportunities to flex their business-building skills in a day job.
- To up your odds of success, deploy the same learning principles you'd use to learn Python or become a project manager — that is: (1) advice, (2) community, and (3) iteration. 10 years ago, I never imagined entrepreneurship would be in my future.
5 years ago, I never imagined being a full-time entrepreneur.
1 year ago, I stepped away from the corporate 9-to-5.
And I haven’t looked back.
Along this journey, I’ve had the opportunity to talk with tons of fellow business-builders. Some who, like me and my wife, have gone all-in. And many who are either testing the waters or generating extra income with a side hustle.
I recently connected with Dexter Zhuang, a former PM at Dropbox who writes the fantastic newsletter, Money Abroad. Dexter has traveled the world as a remote founder and helps others turn their skills into profitable businesses.
Our conversation got me thinking about the entrepreneurial journey. And specifically how entrepreneurship is a skill that few people know but anyone can learn.
If you’re considering a side hustle, this one’s for you.
What is entrepreneurship?
The answer to this question should be pretty straightforward. I mean, we all know what an entrepreneur looks like, right?
In fact, the definitions are all over the place. Harvard Business Review even calls the term “elastic.” It’s no surprise then, that if we can’t even pinpoint the definition of entrepreneurship that making the transition would be difficult.
The standard adage says: “50% of all new businesses fail within a year.”
It’s just a skill
Half of entrepreneurs fail.
But I know plenty of successful entrepreneurs.
And we’ve all heard the garage-to-Fortune 500 success stories of companies like Google, Microsoft, Dell, and Facebook.
So, there’s got to be something bubbling under the surface that allows these entrepreneurs to succeed while others struggle. Dig into the data, you’ll find that serial entrepreneurs are nearly twice as successful as first-time entrepreneurs.
My take on this:
Entrepreneurship is a skill. It’s a tricky skill, requiring the entrepreneur to create something new that adds value and generates revenue. But at its heart, it’s a skill just like learning Python or becoming a project manager.
And if entrepreneurship is a skill . . . then it can be learned.
Let’s pull in learning science
This is Develop Daily, so of course I’m going to reach for learning science.
To help us break down the skill of entrepreneurship, let’s look at some go-to tools for learning any new skill — in this post, I’m going to focus on three.
Advice from folks who have been there and done that.
Community to learn from others who are learning.
Iteration to experiment with new methods and refine your process.
Sure, you can launch a website, trot out your new business, and just give it a go. But if the numbers tell us anything, this is a pretty quick road to struggle (and likely failure). Instead, invest the extra time to really understand what entrepreneurship is and how you can increase your odds of success.
Here’s the playbook:
Advice: How not to make every mistake
I have a simple mantra. Whenever possible, I’d rather learn from someone else’s mistake than make the same blunder on my own.
Admittedly, there are plenty of times when I’m moving too fast or charting new territory, and mistakes can’t be avoided. That said, I’ve managed to dodge a lot of traps by reading accounts from others who have fallen in.
That’s the power of advice.
It’s doubly important in the world of entrepreneurship because most folks don’t have an opportunity to learn from experience before their money is on the line. Most day jobs don’t include the same start-from-scratch dynamic as entrepreneurship.
If you’re making the pivot, advice is your best friend.
Action item: As you start your side hustle, carve out 15 minutes a day to read up on entrepreneurship — specifically the struggles, failures, and experiments of everyday entrepreneurs. Money Abroad is a great source for this. And I’m a huge fan of the recent book from Noah Kagan, Million Dollar Weekend.
Community: How to keep the fire burning
In Develop Daily, we talk all the time about accountability. If there’s no downside to simply walking away from something difficult, most of us will take that option.
That’s why I recommend emerging entrepreneurs find their community. Community will give you an in-built source of additional advice from people who are currently building. It will also give you a powerful source of accountability to keep you moving forward.
Action item: Find your community. It could be a local entrepreneurship group — every major city has several. There’s also a wide range of online communities where entrepreneurs come together to share insights and resources. I’m a part of FounderOS.
Iteration: How to stumble around in the dark until you find the light
My theory: The #1 reason most folks don’t think of entrepreneurship as a skill is because it’s much less linear than, say, learning Excel or how to ride a bike.
Iteration is an essential part of the game.
Instagram: Started as Burbn, pivoted to photo-sharing, became Instagram.
Slack: Failed as a game, but its messaging tool turned into Slack.
YouTube: Began as a dating site, evolved into a video-sharing platform.
Netflix: Transitioned from mail-order DVDs to streaming, revolutionizing entertainment.
One of my favorite posts from Money Abroad is called My $100k Side Hustle Journey. In it, Dexter shares a behind-the-scenes look at five side hustles he’s launched over the years. How they started, how they evolved, and when he decided to walk away.
Reading iteration stories helps you see that success isn’t linear. It’s messy. It’s full of false starts, pivots, and lessons learned along the way. By seeing how others experiment, you get a blueprint for navigating your own journey — without the fear of getting it "right" the first time.
If you’re willing to iterate, you’re already ahead of the game.
Action item: Start iterating now. Instead of staking your side hustle on an all-in bet, deploy a small experiment such as offering a new service to a few friends, selling something on Etsy, or posting about your idea on social media to see how people react. Remember: Small iterations often lead to big breakthroughs.
To Wrap
Your side hustle is waiting.
It’s an opportunity for you to earn extra cash, test out the entrepreneurial waters, and get outside your comfort zone. Who knows, like me you may take the leap into full-time entrepreneurship.
Whether you’re full-time or just kicking around the idea, my #1 suggestion is to take a learner’s approach. Pair your idea with proven tactics grounded in learning science.
Advice: Read up on entrepreneurial success, failure, and lessons learned.
Community: Find yourself some fellow entrepreneurs to build alongside.
Iteration: Experiment like a scientist, placing small bets on what will work.
To close, I’ll make a final plug for a newsletter I believe will truly benefit anyone looking to spin up a side hustle. Money Abroad.
Money Abroad is a weekly newsletter on designing your own money path. Get actionable strategies, case studies, and expert insights on building a portfolio career—so that you can shift from "live to work" to "work to live." Join over 6,000 high-performers working at companies like Meta, Google, Stripe, and more.
Happy building!
-Stephen
P.S. LinkedIn is a great place to learn more about AI. And the LinkedIn Career Content Library features 390 pieces of curated content. Dive in for prompt examples, AI-powered tools, and much more. Happy learning!